Diisopropylethylamine → HCID 59743548, compound

HRID 1947064Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[C:14]1[CH:19]=[CH:18][N:17]=[C:16](S(CCCC)(=O)=O)[N:15]=1)(=[O:4])=[O:3].Cl.[NH2:28][CH:29]1[CH2:34][CH2:33][CH:32]([C:35]([N:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)=[O:36])[CH2:31][CH2:30]1.C(N(C(C)C)C(C)C)C>CCO>[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:28][CH:29]2[CH2:30][CH2:31][CH:32]([C:35]([N:37]3[CH2:38][CH2:39][CH2:40][CH2:41]3)=[O:36])[CH2:33][CH2:34]2)[N:15]=1)(=[O:3])=[O:4]

Participants

Conditions

Temperature: 170 °C

Procedure

4-Methylsulfonyl-1-(2-butylsulfonyl-pyrimidin-4-yl)-1H-indole (250 mg, 0.636 mmol), (4-amino-cyclohexyl)-pyrrolidin-1-yl-methanone hydrochloride (444 mg, 1.91 mmol), ethyl-diisopropylamine (333 μL, 1.91 mmol), and dry EtOH (5 mL) were placed in a vial, sealed, and heated in a microwave reactor at 170° C. for 1 h. The product was concentrated to dryness and purified by column chromatography (5% MeOH in DCM), clear fractions collected and evaporated to dryness, and dried overnight under vacuum. The product was recrystallized from CH3CN and dried under vacuum to provide {4-[4-(4-methanesulfonyl-indol-1-yl)-pyrimidin-2-ylamino]-cyclohexyl}-pyrrolidin-1-yl-methanone (Compound 200, 89 mg).

Workup

customsealed
concentrationThe product was concentrated to dryness
custompurified by column chromatography (5% MeOH in DCM), clear fractions
customcollected
customevaporated to dryness
customdried overnight under vacuum
customThe product was recrystallized from CH3CN
customdried under vacuum

Sources & evidence

ORD record: ord-d3ba24f9a13741f08848e6dab8281a5a
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399462B2

Reaction notes

Loading…